This invention relates to novel silanes having sterically hindered aminohydrocarbyl groups and to a process for their preparation. The sterically hindered aminohydrocarbylsilanes of this invention find general utility as glass-plastic coupling agents, bonding aids, consolidating additives to phenolic binder/foundry mixtures, and adhesion promoters for vinyl plastisols, polyurethane elastomers, and epoxy and acrylic-based inks.
2. The Prior Art
3-Aminopropyl silanes, containing the moiety .tbd.SiCH.sub.2 CH.sub.2 CH.sub.2 N.dbd., have long been articles of commerce. While fairly extensive prior art exists on making such materials and in varying the substituents on either the silicon atom or the nitrogen atom in such materials, relatively little has been done on varying the linkage between the silicon and nitrogen atoms. Thus, for example, there is prior art on a single carbon linkage between silicon and nitrogen atoms (U.S. Pat. Nos. 3,657,303 and 3,673,233), on two carbon linkages (U.S. Pat. No. 2,557,803), on four carbon linkages (U.S. Pat. No. 3,146,250), and even on eleven carbon linkages (U.S. Pat. No. 3,810,843). Even less has been done on varying the carbon linkage from linear to branched or cyclic, although prior art exists on the moieties .tbd.SiCHMeCH.sub.2 N.dbd. (J. Org. Chem., 35, 3879 (1970)), .tbd.SiCH.sub.2 CHMeCH.sub.2 N.dbd. (J. Org. Chem., 36, 3120 (1971), and certain cyclic linkages (U.S. Pat. No. 2,762,823).
A limited amount of work has also been done on preparing unsaturated two and three carbon linkages on silyl tertiary amines (J. Gen. Chem. (USSR), 40, 595 (1970), 41 , 1591 (1971), 45, 81 (1975), and 51 , 311 (1981)). Another unsaturated silyl tertiary amine with the moiety .tbd.SiCH.sub.2 CH=CHN.dbd. is disclosed in J. Gen. Chem. (USSR), 46 , 2074 (1976). The compound (MeO).sub.3 SiCH.dbd.CHCH.sub.2 NHCH.sub.2 CH.sub.2 NH.sub.2 is disclosed in U.S. Pat. No. 2,971,864 (Example 3). None of the above references disclose sterically hindered aminohydrocarbylsilanes.